All roads lead to Dair
by Dair101
Summary: Dan and Blair fan-fic set in what I guess would be season 2 shortly after Dan and Serena break-up again.
1. Chapter 1

A/N First story here guys so any advice and/or reviews would be great. I know this chapter is a little short but I felt like I needed to get the introductory stuff out of the way first so later chapters should hopefully be a bit longer. Let me know what you think

Chapter 1: Breakfast

It all started out like a pretty normal day for Dan Humphrey. He got up in the Brooklyn loft that he now had to himself and quickly got ready, throwing on his standard plaid shirt and jeans. As was tradition on Sundays, he headed over to meet Rufus and Lily for a Van der Humphrey breakfast that undoubtedly would consist mainly of waffles. He hadn`t really wanted to go; the dynamic between Serena and him was still a bit awkward following their break up but Rufus had made him promise to at least make an effort to patch things up between them and move on as friends/family or whatever they were now. He was at least looking forward to seeing Eric. He had been travelling on Cece`s dime for the last few months and Dan had missed his step brother who so often acted as his trusted confidante.

He took a deep breath and composed himself before leaving the elevator, trying to plaster a smile on his face to hide the nerves underneath.

"Dan!" Rufus called out, "So glad you could make it"

Dan sat down his nerves calmed by the fact Serena had not yet arrived, instead he was greeted by smiling faces all round with everyone looking genuinely glad to see him.

"So Daniel, how is your writing going?" Lily inquired and just like that the ice was broken and conversation began to flow with Dan launching into the retelling of his new idea for a novel that he hopes to get published. All was going fine until they were interrupted by the tell-tale sound of the elevator arriving and at once Dan turned towards it.

Striding out of it, confident as ever was Serena with a surprise in tow, Blair Waldorf. Blair was quite possibly the only person he wanted to see less than he did Serena. She embodied everything he hated about the Upper East Side and had always made clear her disapproval of Serena dating a commoner like him from Brooklyn. No doubt she was relieved they had broken up and was now here to make Dan`s life a living hell in return for breaking her best friend`s heart. They both strode in like they owned the place, neither of them casting as much as glance in Dan`s direction.

Serena spoke to Lily saying "Mom, I hope it is alright I brought Blair along."

"Of course it is, she knows she is always welcome," Lily replied "Blair, how are you dear?"

"Very well thank you Lily" said Blair graceful as ever.

They both sat down to join in with the breakfast although the atmosphere was markedly different now with tension hanging in the air. Any forced attempts to make conversation were short lived with the uncomfortable silence returning shortly after.

Dan soon made a move as to leave making an effort to say bye to Serena as he did so but received no response for his troubles. Oh well, he had tried his best and so gave up for now swiftly leaving, vowing to give it another try on another day. Blair however got up and followed him, getting into the elevator with him in silence.

"Humphrey" she spoke commandingly in that infuriating tone of hers "why are you such an idiot?"

"What do you mean now Waldorf?" Dan replied already tired of her jibes.

"Serena is clearly out of your league and yet you let her go _again!_ And somehow you broke her heart in the process although why she cares is beyond me."

"The spark just wasn`t there anymore and I`m sure when she takes the time to reflect on it she will come to the same conclusion. We seemed perfect together but I realised that if we had to try so hard to make our relationship work then maybe it's because it isn`t meant to be."

Having reached the ground floor, Dan strode confidently out, pleased he had been able to convey his feelings to someone even if it was only Blair Waldorf. She remained standing in the lobby for a while longer after he had left reflecting on what he had said with a thoughtful expression.


	2. Chapter 2

A/N Here is the next chapter, hope you find it interesting. Would love to hear your thoughts.

Chapter 2: The end of Chuck and Blair

It had been a couple of weeks since the breakfast and since then Dan had been hiding out in the loft, his promise to fix things with Serena forgotten. To make things worse, despite all this time to himself, he had hit a block with his latest book and he had come to the realisation that without Serena he no longer had a muse who could get his ideas flowing. He had just scrumpled up the latest chapter he was working on, ready to give up, when there was knock on the door.

Dan was surprised at the sound, he had left explicit instructions with his father and Jenny not to bother him and he wasn`t really speaking to anyone else. Nevertheless, he ambled to the door calling out "Alright I`m coming!" to the person who had impatiently continued knocking on the other side of the door.

"This is all your fault Humphrey" Blair strode into the loft the second the door had been opened without waiting for an invitation.

"Hello to you to Blair," Dan retorted sarcastically "What are you doing here, this is Brooklyn remember?"

"Chuck and I broke up, and it`s all your fault!"

"C`mon Blair, I haven`t seen you since the breakfast, how could I be responsible for you breaking up with Chuck," Dan said exasperatedly

"That`s exactly it! I haven`t been able to get what you said to me in the elevator out of my head. I know you were talking about you and Serena but I couldn`t help but feel that it applied to my relationship with Chuck just as well. The spark was…gone. So I…I had no choice but to end things."

Towards the end of her speech she began to falter and Dan could see tears filling her eyes. He stood there for a moment shocked that Blair, the ice-queen, actually had feelings and out of all the people in the world she was showing them to him, Dan Humphrey from Brooklyn.

He stood there unsure of himself for a moment, worried how she would react if he moved to comfort her. Instead he dove behind the sofa and pulled out a movie, Breakfast at Tiffany`s.

"Serena said this was your favourite," he said dangling the DVD invitingly "and for the record I`m sorry about you and Chuck."

"Oh whatever Humphrey, I`m only consenting to watch this with you because I have no one else to turn to, do not think this makes us friends.

"I wouldn`t have it any other way."

As the final credits rolled down the screen Dan came to the realisation that Blair had fallen asleep, obviously exhausted from her arguments with Chuck. They had started off on opposite sides of the blue couch that was a staple in the Humphrey loft but inexplicably as the movie had gone on and with each laugh they shared they moved closer and closer together to the point where their shoulders were almost brushing together. Now asleep, Blair had her head resting on Dan`s chest, he considered waking her but then thought against it afraid off the reaction he would receive for waking an Upper East Side Princess from her precious sleep. Sitting there trying not to move Dan decided to make the most of his time and closed his eyes, fully intending to get some much needed sleep for he had been staying up late recently desperately trying to progress further with his new book.

He needn`t have bothered for he had only just nodded off when he was awoken to the sound of the loft door closing. Blair had packed up her things and gone without saying goodbye; for some reason which he didn`t understand Dan felt a little bit hurt by this but he tried to pass it off saying to himself _"That's what you get for trying to be nice to someone like Blair Waldorf"_


	3. Chapter 3

Chapter 3

He had the feeling she had been avoiding him since the night they watched the movie. It was like she had realised she had removed her armour in front of him and now was afraid to face him. Dan knew, however, she would have no choice tonight. He, along with anyone who was anybody on the Upper East Side, was heading to the party Lily was throwing. He normally tried to get out of these things as much as he could but this time was different. He desperately wanted to see her again, even if just to make sure she was ok. Wow wasn`t that weird, caring about Blair Waldorf of all people.

He headed in the party and straight away was scanning the crowd looking amongst all of the people there only for her. There she was, dressed in the most radiant purple dress that seemed to stand out amongst the, Dan was sure, equally expensive and luxurious dresses around her. Just as he was about to go talk to her, Rufus cornered him, wanting to talk to the son he hadn`t seen for weeks. Dan tried to end the conversation as quickly as possible but by the time he freed himself Blair had disappeared from his sight.

Try as he might, Dan failed to catch sight of again throughout the evening. He had been there for a couple of hours and now, bored by other people`s attempts at making small talk, he decided to escape to the balcony so he could have some peace and quiet.

As he got out there, he realised he wasn't alone. Standing with her back to him was Blair, staring out at the Manhattan skyline. He went up to her and without saying a word just stood there by her side. She looked at him as if to say " _What the hell are you doing here?"_ before returning to her motionless state.

"What`s wrong Blair?"

She stayed quiet for a few moments and just as Dan was about to give up on receiving a response she spoke up "I can't stand it in there right now. Usually I thrive in this sort of situation but today I just feel like screaming at all these people who keep asking annoying questions like "Who`s your date?" I don't have one ok!" She almost shouted these last few lines

"Well if it makes you feel any better I don't have one either," Dan chuckled to himself "and I'm just as bored as you are. Serena always drags me around to say hi to these people and then to those but she, of course, is still not talking to me."

"You can hardly blame her for not talking to you," Blair interjected "you did break up with her remember?"

Dan continued like she hadn't spoken "So do you want to get out of here for a bit?"

"And where do you suppose we go Humphrey?"

"You ever walked through Central Park at night?" he said grinning as he did so.

They had ended up giving up on their walk fairly shortly after they began, neither of them really dressed for walking and Blair's heels in particular making it difficult for her although her stubborn pride refused to let her admit so. Dan had sensed her pain however and take it upon himself to lead to her to a bench.

They were standing in front of it now, Blair looking down on it with something akin to disdain etched across her face.

"I really hope you don't expect me to sit on that Humphrey, this dress probably cost more than your loft!" she exclaimed.

Dan laughed but instead of saying anything just lay down his jacket on the bench and motioned for her to sit. Not used to that sort of kindness, Blair was shocked for a while so instead of coming up with another witty remark she sat down wordlessly.

They sat and talked for ages, finding out they had a lot more in common than they could possibly could have imagined. Neither of them, in Chuck and Serena respectively, had ever had someone who actually laughed at their obscure references from even more obscure movies. It just felt right and so time flew by, both of them forgetting about the harshness of the weather, warmed by their lively conversation.

Their bubble was burst by Dan`s phone going off, Rufus was ringing wondering just where he had disappeared to. Dan managed to avoid giving him an answer on that, simply saying he'll be there in a minute. He got up and turned to offer his hand to Blair. She took hold of it and pulled herself up without thinking about what she was doing.

Dan was just as surprised at her actions as she was but he decided not to comment instead just saying "We better head back then before more people realise we've left."

"Lead the way then Humphrey"


	4. Chapter 4

Chapter 4

A/N hey guys really enjoying writing this story so hope you guys are enjoying reading it! Please review, I love to hear your thoughts.

It had been a week since they had sat in the park talking and laughing together and try as he might he could not stop thinking about her. Her perfume, her clothes, her hand in his…ugh enough. Dan decided he could not go like this so dared to brave the outside world leaving behind the comfort of the loft for the first time in a while.

He had nothing particular to do and, after deliberating for a while, decided to go see Eric who he had not had a proper chance to catch up with after his time at the breakfast was cut short. The Van der Woodsen`s place it was then.

It was only as he was on the elevator on his way up to the apartment that he realised he risked running into Serena again. The very idea had his stomach turning but it was too late to turn back now. And sure enough the doors opened to reveal Serena and…Nate?

"Oh hey Nate, Serena" Dan managed to splutter out, clearly disturbed by the two of them being together.

"Hey Dan, me and Serena were just, you know, hanging out," Nate said awkwardly.

Serena remained quiet as Nate and Dan quickly caught up both trying to ignore the fact that Nate was _"hanging out"_ with Dan`s ex. She nudged Nate on the shoulder, signalling to him that they should go and Nate willingly obliged.

"See you around Dan"

"Yeah see you"

Dan walked past the two of them glad that that particular encounter was now behind him. He headed into the apartment only to find it empty, Eric was nowhere to be found. _Dammit._ Dan could really have done with someone to talk to, especially as seeing Serena with Nate had pissed him off. _It had been a matter of weeks and she had already moved onto Nate._

His thoughts turned, as they had so often recently, to Blair. He didn`t know she would react if he just showed up at her door but right now she was the only person he could think of seeing, in fact she was the only person he wanted to see.

He headed into Blair`s lobby, not caring how she was going to react or what she was going to say.

"Blair" he called out, her doorman had told him she was indeed her.

She walked slowly down the stairs but stopped in her tracks at seeing Dan waiting at the bottom.

"Humphrey! What are you doing here? I told you that we are not friends, you can`t just pop over uninvited!

Unperturbed by her response Dan ploughed on "You know Serena is already basically going out with Nate already?"

"Yeah and? You did break up with her."

"Bit soon though isn't it?"

"That's Serena for you."

"Yeah I guess you're right," Dan admitted dejectedly. "Hey you fancy catching a movie I know this place showing an Audrey Hepburn movie…" Mentioning Audrey to Blair was like mentioning ice cream to a child.

"Ooh yeah ok, wait Humphrey this place isn't in Brooklyn is it?"

Dan just smiled back at her knowingly.

"Fine I better not get mugged or it's your fault!"

This was just what he need to get his mind off Serena for a couple of hours.

Despite Blair's protestations they made it to the cinema in Brooklyn alive and well. She had flat out refused to take the subway insisting instead on her driver taking them together, and idea which Dan eventually gave in to not really wishing to brave the subway during rush hour.

Upon entering the cinema, they brought popcorn, for Dan only of course Blair and buttery popcorn was not going to happen apparently. He sat down a seat away, fully expecting her to want him to adhere to the rules she had set out all that time ago.

"Just this once Humphrey, I'm going to permit you to sit next to me"

Dan smirked and shifted one seat over towards her.

"Although this arm rest remains mine," she added.

The movie started and they both went quiet focussed on what was in front of them. Or at least that was the case for Blair, Dan couldn't stop glancing over at her, her eyes fixated on the screen, not caring how she looked actually making her look more beautiful, in Dan's eyes at least. He laughed at her taking his popcorn and the way her nose crinkled up when a character she disliked appeared on the screen was downright adorable.

It was at that moment Dan realised he was falling in love with Blair Waldorf.


End file.
